Sodium Iodide → N-2-ethyl-cyclohexylamino-3,4,5-trimethoxy-benzoate-hydrochloride

HRID 596235Notes

Reaction equation

HRID 596235 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([O:15][CH3:16])[C:12]=1[O:13][CH3:14])[C:7]([O-:9])=[O:8].Cl.[Cl:18][CH2:19][CH2:20][NH:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[I-].[Na+]>CN(C)C=O>[ClH:18].[CH3:19][CH2:20][N:21]([C:10]1[C:11]([O:15][CH3:16])=[C:12]([O:13][CH3:14])[C:4]([O:3][CH3:2])=[CH:5][C:6]=1[C:7]([OH:9])=[O:8])[CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 13756691N-(2-chloroethyl)cyclohexanamine hydrochlorideHCID 86734526Sodium 3,4,5-trimethoxy-benzoate

Product 1

HCID 88821243N-2-ethyl-cyclohexylamino-3,4,5-trimethoxy-benzoate-hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1.7 g. of sodium-3,4,5-trimethoxy-benzoate 1.45 g. of N-2-chloroethyl-cyclohexylamine hydrochloride and some sodium iodide crystals are added, whereafter 30 ml. of dimethyl formamide are introduced. After cooling toe precipitated crystals are filtered and the filtrate is evaporated. The residue is recrystallized from 96% of ethanol under clarifying with activated charcoal. Thus N-2-ethyl-cyclohexylamino-3,4,5-trimethoxy-benzoate-hydrochloride is obtained. M.p.: 208°-210° C.

Workup

  1. temperatureAfter cooling toe
  2. customprecipitated crystals
  3. filtrationare filtered
  4. customthe filtrate is evaporated
  5. customThe residue is recrystallized from 96% of ethanol

Sources & evidence

ORD record
ord-eaf5569218344429b65035dc5a7984e5
Source dataset
uspto-grants-1977_03
Patent number
US04010193

Reaction notes

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